Jonathan T Penny
Founder at Stache Technology
Engineering leader with experience at Google, Twilio, and Wayfair. MBA from University of Illinois | AWS Certified | Building AI-powered knowledge management tools.
Recent Posts
View all →Understanding RAG: A Practical Guide for Engineers - Part 2: Vectors, Embeddings, and How RAG Actually Works
Understanding RAG Part 2: How vectors capture meaning, why semantic search beats keywords, and the three stages that make retrieval-augmented generation work.
Understanding RAG: A Practical Guide for Engineers - Part 1: What is RAG and Why Should You Care?
RAG quietly powers most production AI apps. Learn why retrieval-augmented generation beats fine-tuning for customer support, search, and document Q&A.
Enterprise AI Security: Why You Need a Layer Between Your Data and Claude
How Stache's middleware architecture addresses the security gaps exposed by Claude Cowork's prompt injection vulnerabilities.
OAuth 2.1 Dynamic Client Registration for AWS BedrockAgentCore
A CloudFormation template implementing OAuth DCR for BedrockAgentCore Gateway with Cognito.
Running Stache on AWS with Stache Serverless
A production-ready serverless RAG system built on AWS - Lambda, S3 Vectors, DynamoDB, and Bedrock.
Fractional CTO
Go Fractional- • Part-time CTO leadership for startups and growing companies that need senior technical judgment but aren't ready for a full-time executive hire
- • Technical strategy and architecture: deciding what to build, what to buy, and what to defer
- • Practical AI adoption: LLMs, RAG, and agents built to run in production, with clear guidance on cost and reliability
- • Cloud infrastructure, reliability, and cost control, drawing on SRE leadership at Google and global compute at Twilio
- • Engineering team building: hiring, org design, process, and coaching new managers
- • Board, investor, and due diligence support: roadmaps and technical assessments that non-technical stakeholders can follow
Founder
Stache Technology- • Building AI-powered knowledge management tools for enterprises
- • Developing RAG pipelines and semantic search infrastructure
Engineering Manager
Twilio- • Led a team of engineers focused on migrating from data center to AWS
Engineering Manager
Google- • Led a team of engineers focused on improving developer velocity in the testing space
Senior Engineering Manager
Wayfair- • Led a team building an event-driven platform for finance engineering using Python and Kafka
- • Implemented software updates predicted to drive more than $200M in additional yearly profit
- • Built an event-based platform to decouple functions from a legacy monolith for SAP migration
DevOps Leader
QsrSoft- • Architected and scaled AWS infrastructure to analyze streaming data from 14,000 US McDonald's restaurants, peaking at 500 tps
- • Drove major initiatives including infrastructure as code, CI/CD, agile SDLC, migration to GitHub and Jira
- • Led migration of EOL applications from on-premise to AWS, realizing several $M in additional revenue
Director of Technology
myFootpath- • Reported to CEO and managed all technology for a company with > $10M in revenue
- • Led team to build new product enabling complete business model pivot from call center to self-service
- • Reduced technical headcount from 7 to 1 through automation and complexity reduction
CTO/Founder
Socialhood- • Founded Socialhood, a social network for the neighborhood
- • Architected the original concept and led a distributed team that built out the application
Director of Engineering
Working Person's Store- • Created comprehensive technology strategy for INC 500 company with $10M in revenue
- • Consolidated vendors, migrated telephony to VOIP, implemented ticketing, managed call center move
Master of Science in Computer Science
Western Governors University- • Focus on Machine Learning and Artificial Intelligence
Master of Business Administration (MBA)
University of Illinois- • Focus on Strategic Leadership, Entrepreneurship, and Strategic Innovation
- • Partnered with medical and engineering students to produce GTM plan for new medical device